10 Best Vacation Rentals in Sanford - Holiday Lettings - Cabins

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143 Vacation rentals

24

Apartment rental in Sanford

Central Florida / Sanford

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Enjoy all the lively attractions and scenic beauty of this quaint Florida town from this 2-bedroom, 1-bathroom vacation rental apartment, which comfortably sleeps 6 in Sanford. This 2nd-story unit offers a beautiful, residential location, a handsome garden, patio and de …see more

from $125 / night

$875 / week

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avg. 9 minutes

from $125 / night

(4) Excellent 

23

Sanford Vacation cottage rental

Central Florida / Sanford

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 24 mi
  • Swimming pool
  • Child friendly
Welcome to FLOATING COTTAGE . . . charming and unique houseboat vacation rental on the St. Johns River . Imagine relaxation, gently afloat in a quiet, clean-water designated marina in Sanford, Florida. Poised to delight, Floating Cottage provides a peaceful environme …see more

from $135 / night

$850 - $985 / week

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from $135 / night

(2) Excellent 

27

Vacation home in Sanford

Central Florida / Sanford

4 13 3 nights min

  • 4 bedrooms
  • sleeps 13
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
A quiet house with a large cabin feel, tucked away from the hustle and bustle of Orlando and Daytona Beach but is within short driving distances from some of Florida's amazing springs and nature walks! The house boast an amazing view of the Saint John's river, the Lake …see more

from $285 / night

$1,700 / week

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avg. 1 hour 3 minutes

from $285 / night

24

Vacation home in Sanford

Central Florida / Sanford

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Take the family on a trip to an Orlando oasis when you stay at this 3-bedroom, 3-bathroom vacation rental home that sleeps 8 in Sanford. Sitting just outside of the city, this home offers all the comforts of home paired with an ideal location to reach the excitement of …see more

from $145 / night

$1,015 / week

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avg. 1 hour 19 minutes

from $145 / night

(1) Excellent 

16

Bungalow rental in Sanford

Central Florida / Sanford

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 35 mi
  • Air conditioning
  • Private garden
COMPLETELY RENOVATED BUNGALO WITH QUEEN SIZE BEDS IN BOTH BEDROOMS. ALL NEW FURNITURE AND BEDDING. COMPLETELY NEW KITCHEN AND BATHROOM. WASHER AND DRYER IN LAUNDRY ROOM. LARGE BACK YARD. NICE FRONT PORCH WITH VIEWS OF CITY PARK. REAR DECK WITH GRILLE. FIRST TIME ON THE …see more

from $130 / night

$675 / week

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from $130 / night

24

Sanford Vacation apartment rental

Central Florida / Sanford

2 3 3 nights min

  • 2 bedrooms
  • sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
Gather your loved ones for a relaxing getaway to this 2-bedroom, 1-bathroom vacation rental apartment in Sanford, Florida. You’ll love staying at this quaint property that features large windows, high ceilings, and beautiful french doors that open to a great balcony sit …see more

from $109 / night

$763 / week

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avg. 7 minutes

from $109 / night

24

Sanford Vacation studio accommodation

Central Florida / Sanford

Studio 2 3 nights min

  • Studio
  • sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
Up to 2 guests can experience the beauty of Florida from this 1-bathroom vacation rental studio in the heart of Sanford. This luxurious space is perfect for a secluded getaway and features elegantly stocked cupboards, plush furniture, and a complete kitchenette. Moments …see more

from $99 / night

$693 / week

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avg. 9 minutes

from $99 / night

24

Sanford Vacation home rental

Central Florida / Sanford

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Elevate your next trip to central Florida by staying at this pristine 3-bedroom, 2-bathroom vacation rental townhouse in Sanford. This 1,920-square-foot unit sleeps 7 travelers and offers access to the community pool. Eat with the locals in downtown after a visit to the …see more

from $123 / night

$861 / week

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avg. 9 minutes

from $123 / night

24

Vacation home in Sanford

Central Florida / Sanford

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Visit the historic town of Sanford from this vintage 3-bedroom, 3.5-bathroom vacation rental house with 1,400 square-feet of living space and sleeping accommodations for 6. Located just a few minutes from Main Street, enjoy quick access to a plethora of restaurants, ant …see more

from $209 / night

$1,463 / week

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avg. 9 minutes

from $209 / night

27

Vacation apartment in Sanford

Central Florida / Sanford

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
Nestled under a 100-years-old live oak tree, 'Chef's Suite at Live Oak,' an executive 1-bed vacation rental apartment, offers comfort, intimacy, and upscale living for 2 guests in Sanford, FL. Enjoy a peaceful resort-like experience at this quiet, end-unit, with all the …see more

from $99 / night

$693 / week

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avg. 1 hour 2 minutes

from $99 / night

Great rentals within 20 miles that match your search

Distance approx 10.21 miles from Sanford

7

Home rental in Orange City

Florida / Orange City

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
We are pleased to offer our 3 bedroom family house in Orange City, Florida. The house is 1,928 sqft and is set on 5 acres of land. There are three bedroom one of which has an en-suite bathroom. All the bedrooms have king-size beds and there is a sofa bed in the living r …see more

from $450 / night

$2,940 / week

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from $450 / night

Distance approx 12.62 miles from Sanford

18

Maitland Vacation home rental

Florida / Maitland

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Child friendly
This beautiful 3 bedroom, 2 full bathrooms home is located in a lovely and quiet community. Close to shops, restaurants, just minutes away from Winter Park. Great for Disney vacations, corporate housing, holidays, UCF, or just to relax in sunny Florida. While in Florid …see more

from $200 / night

$1,300 / week

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from $200 / night

Distance approx 13.73 miles from Sanford

18

Home rental in Maitland with swimming pool

Florida / Maitland

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly
Close to everything. Minutes off major highway I-4. 2 bedrooms, 2 baths. Large living area, fully stocked kitchen, laundry, dinning room, great private porch & pool area. Plus outdoor shower. 30-40 minutes to attractions. 60 minutes to the beaches. Our guests ca …see more

from $150 / night

$950 / week

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from $150 / night

Distance approx 16.81 miles from Sanford

27

Vacation home in Winter Park

Central Florida / Winter Park

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
Your own private unit includes 1 master bedroom with Queen bed Full Kitchen with stove, refrigerator, microwave, coffee maker 32" flat screen tv. Access to Washer/dryer Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close t …see more

from $75 / night

$499 / week

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avg. 2 hours 18 minutes

from $75 / night

Distance approx 11.3 miles from Sanford

22

Vacation home in Orlando

Central Florida / Orlando

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Room for rent & furnished common areas to share in Beautiful Huge newer Home in Prestigious Victoria Park Community. Only 35 minutes to Universal & Orlando & same time to Daytona beach for best of both worlds. Amenities include; Cable TV & Internet/WIFI, nearby Golf Co …see more

from $200 / night

$1,100 / week

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from $200 / night

Distance approx 10.46 miles from Sanford

19

Vacation home with swimming pool in Longwood

Florida / Longwood

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
If you need a beautiful vacation home away from home in centrally located Longwood, Florida between Disney World and Daytona Beach with a concierge service come stay with us. This 1200 Sq feet 2 bedroom 2 bathroom home is elegantly furnished down to the last detail. T …see more

from $129 / night

$775 / week

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avg. 54 minutes

from $129 / night

Distance approx 15.65 miles from Sanford

(1) Excellent 

60

Vacation b&b with golf nearby in DeLand

Florida / DeLand

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Child friendly
Swiss-Floridian Bed and Breakfast homestay in Deland. A warm welcome to all of our guests. A beautiful, cozy home in nature, privately located on a quiet street is waiting for your visit. Our home is only 5 min. walk to downtown Deland, restaurants, parades, Stetson …see more

from $95 / night

$665 / week

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avg. 1 hour 33 minutes

from $95 / night

Distance approx 15.65 miles from Sanford

61

DeLand Vacation b&b rental

Florida / DeLand

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Child friendly
Swiss-Floridian Bed and Breakfast homestay in Deland. A warm welcome to all of our guests. A beautiful, cozy home in nature, privately located on a quiet street is waiting for your visit. Our home is only 5 min. walk to downtown Deland, restaurants, parades, Stetson …see more

from $69 / night

$483 / week

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avg. 1 hour 33 minutes

from $69 / night

Distance approx 19.28 miles from Sanford

24

Orlando Vacation apartment rental

Central Florida / Orlando

1 3 30 nights min

  • 1 bedroom
  • sleeps 3
  • 30 nights min
  • Suitable for children age 5+
  • Air conditioning
Come and enjoy this quaint downtown Orlando vacation rental apartment, ideally located within easy reach of downtown attractions. This 1-bedroom, 1-bathroom apartment can accommodate up to 2 guests and includes a kitchen, wireless internet access, cable TV, air conditio …see more

from $99 / night

$693 - $1,393 / week

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avg. 14 minutes

from $99 / night

Distance approx 16.2 miles from Sanford

19

Vacation studio rental

Florida / Wildwood

Studio 8 7 nights min

  • Studio
  • sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
It can't get any better! A brand new 3 bedroom condo on the boardwalk in Wildwood, NJ. You can enjoy the ocean view from the large porch, watch the fireworks, or observe the boardwalk activities from the 2nd story porch. Once inside, you close out the sounds of the boar …see more

from $400 / night

$2,800 / week

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from $400 / night

Distance approx 15.32 miles from Sanford

(2) Excellent 

13

Vacation home in Winter Park

Central Florida / Winter Park

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 88 mi
  • Child friendly
  • Air conditioning
Furnished with original furniture from the 1950's era in a home built in 1955 with original wood floors, bathroom tile, plaster walls and kitchen cabinetry. Clean lines, simple and comfortable. FURNISHED Mid Century Modern Short/Long term rental located in Olde Winter …see more

from $143 / night

$1,000 / week

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from $143 / night

Distance approx 5.42 miles from Sanford Show on Map

14

B&b rental in DeBary with shared pool

Florida / DeBary

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This listing is for one private bedroom. Our home is a split level with the upstairs reserved for guests. We reside in the other side of the home downstairs. The upstairs has it's own kitchen with a microwave, toaster, coffee maker, and a fridge. There is also a small l …see more

from $25 / night

$200 / week

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from $25 / night

Distance approx 14.04 miles from Sanford

27

Vacation home with swimming pool in Goldenrod

Florida / Goldenrod

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Up to 10 guests can share a very special getaway at this 4-bedroom, 2.5-bathroom vacation rental home in Orlando! Friends, families, or business travelers will be able to comfortably spread out in this spacious, 2,700-square-foot home. With a private pool and grassy bac …see more

from $255 / night

$1,785 / week

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avg. 1 hour 2 minutes

from $255 / night

Distance approx 16.9 miles from Sanford

(3) Very Good 

22

Winter Park Vacation home rental

Central Florida / Winter Park

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
Your own private unit includes 1 master bedroom with Queen bed Full Kitchen with stove, refrigerator, microwave, coffee maker 32" flat screen tv. Access to Washer/dryer Comfortable & Clean 1bd/1bath home with convenient location in historic Winter Park yet very close t …see more

from $80 / night

$530 / week

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avg. 2 hours 18 minutes

from $80 / night

Distance approx 17.87 miles from Sanford

10

Townhouse rental in Winter Park

Central Florida / Winter Park

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
You’ll love this place! Recent renovations makes this mid-century modern cottage feel like a dream and you can't beat the location! Smart TVs (no cable). Modern furniture, full kitchen with Quartz counter tops and Slate appliances. Everything is less than 2 years old. …see more

from $130 / night

$910 / week

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from $130 / night

Distance approx 16.02 miles from Sanford

34

Vacation home in Apopka

Florida / Apopka

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
MONTHLY RATES 4 weeks from $2200 - $2400. Please CHECK WITH OWNER! Designer touches throughout this beautifully renovated 1950s home in the upscale Bear Lakes area. 3 bedrooms, 2 bathrooms, spacious living room/dining area. Private screened porch overlooking private …see more

from $135 / night

$800 - $1,100 / week

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avg. 3 hours 49 minutes

from $135 / night

Distance approx 18.09 miles from Sanford

18

Vacation apartment in Orlando

Central Florida / Orlando

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Child friendly
  • Air conditioning
This Is A Beautiful Apartment Located Above A Detached Garage At A Private Residence. Completely Private Entrance And Parking. The Apartment Sits On A Corner Lot With A Balcony And Great View Of Lake Formosa. The Apartment Is Fully Equipped With Everything You Need Incl …see more

from $115 / night

$750 / week

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from $115 / night

Distance approx 17 miles from Sanford

44

Apartment rental in Orlando

Central Florida / Orlando

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Nearest beach 72 mi
  • Child friendly
  • Air conditioning
The ground floor apartment of a duplex which is fully furnished, has a kitchen, bathroom with shower, laundry machines, cable television, wireless internet, and off street parking. Can sleep up to 3 people comfortably. Conveniently located to Orlando, College Park, Wi …see more

from $112 / night

$735 / week

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from $112 / night

Distance approx 8.37 miles from Sanford

24

Home rental in Osteen

Florida / Osteen

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
Leisurely days and sunshine rays are ready to show you the best of Osteen at this newly updated 4-bedroom, 2-bath vacation rental house! Ideal for up to 8 travelers, this home boasts 1,828 square feet of high end living space and a private dock on St. Johns River. When …see more

from $175 / night

$1,225 / week

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avg. 1 hour 2 minutes

from $175 / night

Distance approx 17.17 miles from Sanford

(2) Good 

20

Winter Park Vacation home rental

Central Florida / Winter Park

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
This is a great little neighborhood chock full of local businesses, great people, nice neighbors and just a nice homey feeling. I can't get enough of the Main Street (Edgewater Dr.) running through, you have everything from some pretty great restaurants, plenty of yoga …see more

from $80 / night

$510 / week

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avg. 2 hours 18 minutes

from $80 / night

Distance approx 18.14 miles from Sanford

18

Fairvilla Vacation home rental

Florida / Fairvilla

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
One of our most popular tiny houses, this quaint tiny home is filled with charm. A large deck with a seating area makes The Lake House perfect for relaxing after a long day of experiencing all that Orlando has to offer. This tiny home comfortably sleeps three adults, or …see more

from $68 / night

$476 / week

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from $68 / night

Distance approx 19.63 miles from Sanford

37

Guest house rental in Orlando with golf nearby

Central Florida / Orlando

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Car not necessary
  • Air conditioning
  • Private garden
Urban cool meets childhood fancy in this downtown boutique bungalow in the Country Club of Orlando. The Little Treehouse is the perfect Central Florida getaway for two in this separate 260 sq. ft. second floor renovated 1926 carriage house. Conveniently located five min …see more

from $110 / night

$770 / week

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from $110 / night

Distance approx 18.32 miles from Sanford

11

Vacation home in Orlando

Central Florida / Orlando

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
Temporary Rental single family home 5 mins from Disney property. Beautiful well mainted single story home in quiet upscale neighborhood. 2 bedrooms and 3 bathrooms (master bedroom queen bed and second bedroom twin bed). Entire home furnished and very clean. 5 mins from …see more

from $315 / night

$2,200 / week

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from $315 / night

Distance approx 18.14 miles from Sanford

12

Vacation home in Fairvilla

Florida / Fairvilla

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
This 2018 tiny house has all the bells and whistles! Projector screen TV, surround sound speakers, heated tile floors, full size refrigerator and stove. When most people think of tiny houses they think of a loft you have to crawl into... Well yes there is one of those w …see more

from $74 / night

$518 / week

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from $74 / night

Distance approx 5.69 miles from Sanford Show on Map

7

Vacation home in DeBary

Florida / DeBary

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Clean, bright, and spacious remodeled spilt plan house on a small lake. Sanford Int Airport only 13 miles away. Easy access to the Sunrail/highways. We are half way between Disney and Daytona Beach. Discover the Natural side of Florida. We have gorgeous Springs (Blue, G …see more

from $125 / night

$700 / week

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from $125 / night

Distance approx 16.27 miles from Sanford

35

Winter Park Vacation villa rental

Central Florida / Winter Park

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Lakeside, on the shores of Lake Killarney, is in the exclusive village town of Winter Park (32789). You are 7 min to downtown Orlando, 20 min to Universal/ Disney. A 5,700 sq. ft family estate home with 285 ft of shoreline situated in an eco-sanctuary of rare birds & …see more

from $595 / night

$3,995 - $6,300 / week

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from $595 / night

Distance approx 10.82 miles from Sanford

22

Condo rental in Longwood

Florida / Longwood

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
If you're looking for European paradise, you don't have to travel across the pond - make your way to this Longwood vacation rental unit instead! This 2-bed, 1-bath condo sleeps 4 and will feel more like your very own English manor; with over 1,000-square-foot interior d …see more

from $95 / night

$665 / week

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avg. 14 minutes

from $95 / night

Distance approx 15.97 miles from Sanford

20

Vacation home in Alafaya

Florida / Alafaya

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 60 mi
  • Child friendly
  • Air conditioning
This beautiful home is located 5 min. from UCF and shopping. Throughout the house you will observe original European paintings for your delight with rich colors and lively figures. The house has newly remodeled kitchen with granite countertops. The bathroom has natura …see more

from $125 / night

$750 - $1,016 / week

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from $125 / night

Distance approx 5.42 miles from Sanford Show on Map

12

Vacation b&b with shared pool, golf nearby in DeBary

Florida / DeBary

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This rental is a single room in our home. It is located upstairs and is private. Our home is located in central Florida and has many activities close by. The attraction area begins about 40- 45 minutes south on Interstate 4 (our home is about 5 minutes from the exit). T …see more

from $25 / night

$200 / week

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from $25 / night

Distance approx 5.42 miles from Sanford Show on Map

(3) Excellent 

12

Vacation b&b in DeBary

Florida / DeBary

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a shared residence.The upstairs is reserved for guests and private. We live downstairs with our dog Some areas are common areas such as the dining room, kitchen, and back patio. We have hosted other families and will give you as much or as little interaction as …see more

from $50 / night

$225 - $505 / week

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from $50 / night